Reaktion #446931

Reaktionsgleichung

ammonium chloride

N-Butyllithium

2-methylthiophene

oxetane

→

title compound

Ausbeute 17.6%

5-Methyl-2-thienylpropanol

Ausbeute 17.6%

Lösungsmittel

hexane

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 22.5 h
3. 3
   Extraktionthe mixture extracted with diethyl ether (3×200 ml)
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated in vacuo
6. 6
   Sonstigeto give an oil
7. 7
   SonstigePurification by FCC on silica gel with cyclohexane-diethyl ether (1:1) as eluent

Vorschrift

N-Butyllithium in hexane (1.5M; 35.6 ml) was added dropwise at room temperature under nitrogen to a solution of 2-methylthiophene (5.0 g) in dry THF (50 ml). After stirring for 2.25 h, oxetane (4.42 g) in dry THF (15 ml) was added dropwise and stirring continued for 22.5 h. Saturated ammonium chloride solution (200 ml) was added and the mixture extracted with diethyl ether (3×200 ml), dried and evaporated in vacuo to give an oil. Purification by FCC on silica gel with cyclohexane-diethyl ether (1:1) as eluent gave the title compound as a pale orange oil (1.4 g). T.l.c. (cyclohexane-diethyl ether 1:1) Rf 0.31.

Quelle